See "Old Florida" in Oldsmar

Where the waters of Tampa Bay, the Gulf of Mexico and Lake Tarpon come together at the north end of Old Tampa Bay, you’ll find Oldsmar. Fun fact: Oldsmar was originally named R. E. Olds-On-The-Bay after its founder, automobile maker Ransom E. Olds—the Oldsmobile namesake.

Oldsmar is a particularly fun place to visit during its signature events. The town's Oktoberfest, offering authentic German food, German beer, live entertainment and a Munich-style tent, is known as one of the best in Central Florida, while the three-day Freedom Fest is a family-friendly, Memorial Day street festival. Oldsmar's longest-running festival is Oldsmar Days, featuring a bevy of classic cars, live rock 'n' roll, a carnival and parade. If you love horse racing, check out Tampa Bay Downs, the area's only Thoroughbred horse track, with live racing from December through May.

Bonus fun fact: This town has more parks per square mile than any other city in the state. Soar above the tree tops of Mobbly Bayou Wilderness Preserve on a zip line tour with Empower Adventures Tampa Bay, or paddle a canoe along trails in the bay and enjoy the shore’s undeveloped parkland and natural beauty.